Tina Fey: Miss Tina Regrets

One Sunday back in September 2008, the television show 30 Rock—and therefore Tina Fey—had one of those crazy, ebullient awards-show nights that linger in the memory: a clean sweep of the major prizes in the comedy category at the Emmys, including Outstanding Writing for a Comedy Series for Fey herself for an episode called “Cooter.” That Tina Fey could so blithely accept an award before an enormous television audience for an episode she named after a pet word for her vagina is but one small testament to how completely she has managed to bend the world of television toward her particular brand of superfunnysmart feminism.

When she got up to accept, she looked startlingly gorgeous in a dark-plum David Meister gown—“the vampiest thing I have ever worn,” she says. Someone handed her the statue, and she shouted, “Oh, nerds!” What no one could see on television that night was that the lining of her dress had been slowly creeping up her legs, and by the time she was onstage, it was bunched up around her hips. “You look at pictures of me from the pressroom backstage,” she says, laughing, “and I have these weird lumps; it looks like I had liposuction that went bad.”

I happened to be staying at the Four Seasons in Beverly Hills that weekend, and on Monday morning I was at the gym bright and early—the only person there. Until Tina Fey walked in. All traces of the previous evening’s glamour were gone. In fact, the person before me looked nothing like the person who’d been on TV. She could have been any harried working mother who had dragged herself to the gym in rumpled workout clothes, clutching a cup of coffee as if her life depended on it. I was dying to congratulate her but could not bring myself to, partly because I was afraid it wasn’t her. When I mention this one day on the set of 30 Rock in December, she clearly remembers that morning, too. “Did I actually work out?” she asks. “Or was I just standing by the beautiful samovar of Gatorade eating the tiny free muffins?”

Normal Girls

Journalists are constantly asking Tina Fey if she is totally surprised by her success. This is partly to do with the fact that she is the most unlikely glamour-puss ever to triumph on such a grand scale: a glasses geek turned writer turned TV star turned movie star turned presidential-election-year sensation turned household name. “I don’t fit the mold,” she says. “In this country, success usually happens when you are 22 and six feet tall. Clearly, by asking that question they are kind of letting me know that I am an aberration.”

A friend of mine recently said this: “Her existence is such a relief.” By which she meant that women of a certain age who are cool, funny, and smart but who are by no means fabulous—who are in fact befuddled by much of what passes for fabulous these days—are relieved to see Fey celebrated as such. When I share this with Fey, she says in the most sincere tone imaginable, “That is such a lovely thing to say.” She thinks it over for only a second. “I feel like I represent normalcy in some way. What are your choices today in entertainment? People either represent youth, power, or sexuality. And then there’s me, carrying normalcy.” Pause. “Me and Rachael Ray.”

Hand-Me-Downs

Tina Fey was born near Philadelphia in 1970. (She turns 40 in May.) When she was in grade school, a cousin gave her some hand-me-downs that included a “colonial-lady” Halloween costume. “It consisted of a bonnet,” says Fey, “and a burlap apron and a long skirt. And I would just wear it sometimes after school.” She stares at me and blinks a couple of times. “As an outfit.” Another pause. “It was the Bicentennial! People were excited!”

The Feys were a funny family. And they loved funny TV, which they often all watched together: Monty Python, Saturday Night Live, The Honeymooners. Little Elizabeth Stamatina had her own intense fixations on certain TV ladies: Shirley (from Laverne & Shirley), Stockard Channing, Wonder Woman, anyone from The Love Boat. “When I was really young, I loved the movie White Christmas—I still do—and I thought Rosemary Clooney was so pretty. When I was like nine I would tell people, ‘You know who I kind of look like? Rosemary Clooney.’ I couldn’t look less like Rosemary Clooney, who had big blue eyes and blonde hair. But I wanted to put it out there to see if anyone would bite.”

Suddenly she remembers something and whips out her iPhone. She recently found some old photographs of herself at her parents’ house. In one, from fifth grade, she looks so much like a boy—“an unfortunate boy,” she says—that I have trouble believing it’s actually her. “I have on a boy’s hand-me-down disco shirt,” she says. “And I’m wearing a blazer. But down below, I had on a chocolate-brown velour A-line skirt, tights, and Hush Puppies. But you don’t see the skirt in the picture. This is where I first learned the lesson, How will the outfit be framed on-camera? A lesson you take with you to the Oscars because you look at a dress and think, No one’s going to see anything but the top of it.” She holds up her iPhone. “This outfit was not properly framed for the cam-er-aaa.”

She flicks the screen with her finger, and up pops another gem from the same era. “This one might be good for VOGUE,” she says. “My mom had taken me to a haircut-training school, where apparently they cut my hair by folding my head in half and trying to cut out a heart.” What’s up with the collar on that shirt? I ask. “Again, these are all hand-me-downs. I think that’s a Peter Pan collar. You could put that on Built by Wendy and sell it for $260—the whole look.”

Knockers Up

Fey, who is half Greek, grew up in Upper Darby, Pennsylvania, a very Greek suburb of Philly. Though her mother favored comfort and natural fibers in the seventies, most of the women in the neighborhood preferred a zestier presentation: Candie’s, red nail polish, dark eyeliner, maybe a tight-fitting animal print, décolletage, hair piled up. “I still kind of like all that stuff,” says Fey. “It’s certainly not my day-to-day thing, but it does appeal to me every now and then. Part of it is what works with your body. I don’t have a WASP body. Preppy doesn’t work on me at all. There’s something about the Greek thing where there’s only, like, two speeds. If you put me in something conservative, it looks matronly. And if you cut it down to here”—she gestures to her navel—“it looks slutty.” For example, the character Fey played in Baby Mama, a film set in Philadelphia, was meant to be a WASP. “The woman who did the costumes tried to put me in these Waspy clothes, and it just didn’t work. I feel like ethnicity and fashion go together. So, yeah, knockers up and tight skirts. Somehow it’s better.”

One day when Fey was in high school, she went to the Springfield Mall with her friend Sandee and came upon an outfit that spoke to her inner bad girl. “Talk about the power of clothes to make you feel like more than you are,” she says as if she had just tried the outfit on this morning. “It was a white denim suit: a fitted skirt above the knee, and then the top was a jacket with a turned-up collar that you could zip all the way up. It probably had three-quarter sleeves, and it was very fitted through the waist. I remember thinking, I look fantastic in this. I have really come into my own in my white denim suit.”

Everything She Knows About Fashion . . .

Fey was a total drama-club geek in high school, but when she went to the University of Virginia she intended to give all that up, get serious, and become an English major. “But then I got there and realized there was no need to; I just declared a drama major, which was much easier.” It was there, in the costume department, that the seeds of her fashion education were planted. “I feel like any understanding I have of clothes and their impact came from the theater. I worked in the costume shop at UVA, and then later, when I was a writer at SNL, I became good friends with Dale Richards and Tom Broecker, the guys who do the costumes. Everything I know about proportion and detail and period—as opposed to real-life fashion, all of which I find fascinating—I learned from those guys.”

Broecker is the costume designer for SNL and 30 Rock, and he and Fey also work together on her red-carpet looks. “She’s so funny and so smart, and she gets all of it,” he says. “She understands the need for looking a certain way and at the same time understands the trappings of all of that. She has subtly changed what women look like on a weird level: the acceptance of the dark-haired girl, the acceptance of the sexy librarian, the girl with the glasses who’s smart but can be pretty.”

Mom Jeans

After five years in Chicago with the Second City improv group, Fey moved to New York City in 1997 to write for SNL. She lived ever so briefly in SoHo. “I think part of picking where you live in New York is accepting who you are. Really looking at yourself and going, ‘Yeah, I’m not cool enough for the West Village.’ ” She settled on the Upper West Side. “The birthplace of fashion,” she deadpans.

One day the writers at SNL were all sitting around the writers’ room when the legendary creator of the show, Lorne Michaels, walked in, looked around, and said, “There’s not one stylish person that works for this show.” And he was right, says Fey. Back in the seventies, most of the cast and the writers put some effort into looking cool. But now, at the tail end of the grunge period in the nineties, all the writers thought it was self-indulgent to be concerned with fashion. Fey herself kept her hair short and was 30 pounds overweight, which she blames on Chicago. “It’s cold, and the food is really good, and everyone’s a little bit beefier for the most part.”

But when Jimmy Fallon arrived, a fashionable breeze began to blow through the halls of Rockefeller Center. Fallon started dating Tara Subkoff and going to Imitation of Christ shows. (“I get invited to fashion shows,” says Fey, “but I feel like I’d get busted if I went to them. People would be like, Who you tryin’ to be?”) Fey, who finally had some money in her pocket, longed to buy some decent clothes. Then one day she caught an unflattering glimpse of herself on videotape and decided enough was enough. “I’d better sort of head this off now,” she told herself, and went on a diet. It was around this time that three big things happened. Lorne Michaels asked her to audition for “Weekend Update” (“That was life-changing”); she became the first female head writer in SNL history; and she had a fire in her apartment and had to run out to buy an emergency pair of jeans one day for work. “It was right before the low-rise thing kicked in officially, and I inadvertently bought these jeans, and they had this enormous rise. And I was going around the office complaining about them all night, joking about it, and Maya Rudolph and I started singing a little Mom Jeans song. We just goofed around, and I wrote that up very quickly.” To coin a phrase is something special. To name a fashion faux pas so that others may avoid it? That’s God’s work. “The first step,” says Fey, with mock gravity, “was admitting I had on Mom Jeans.”

The Skinny

“I don’t weigh myself. I just go by if my clothes fit. I try not to participate too much in the incredible amount of wasted energy that women have around dealing with food. I just feel like being healthy is sort of a job requirement to be on TV, and being a writer is so much coping with fatigue and stress, and you just eat. You eat to stay awake.” Since the day Fey went in front of the camera, she has kept the weight off. “I’ve never gone back up,” she says. “Well . . . I have had a baby. I gained 35 pounds.” She laughs. “And had a five-pound baby.

“People will say, ‘Oh, fashion magazines are so bad, they’re giving girls a negative message’—but we’re also the fattest country in the world, so it’s not like we’re all looking at fashion magazines and not eating. Maybe it just starts a shame cycle: I’m never going to look like that model, so . . . Chicken McNuggets it is! And conversely, I don’t look at models who are crazy skinny and think I want to look like that, because a lot of them are gigantic, with giant hands and feet. Also, my dad is an artist—a painter by hobby—and I constantly would see realistic nudes. Because we were raised around art and went to museums and the women I grew up around were curvy . . . there wasn’t this value on skinny, skinny, skinny. Curvy was clearly meant to be the winner. I go up and down a few pounds with a relative amount of kindness to myself. And I have a daughter, and I don’t want her to waste her time on all of that.”

Going Rogue

Tina Fey has only recently splurged on herself with all that money she’s been making. She bought a much fancier apartment not far from where she lives; it is in the midst of a major renovation. She has even hired a decorator. She also bought a “little house” in the country, but she won’t say where, because “I don’t want anyone to come there and try to kill me.” Ever since her devastatingly funny Sarah Palin impressions, she has for the first time in her life attracted unwanted attention—and hate mail. “People started projecting politics onto me,” she says. “There are people who hate me now because of that.” Fey’s parents are Republicans, and she herself is an Independent. “The partisan nature of politics continues to appall me. I’m almost paralyzed by my inability to see things in black-and-white. I encountered a lot of hard-core Democrats who are just as rabid and hateful, and I found that just as shocking. It was scary to be in that world of politics. I felt uncomfortable to be in that discussion. The weird thing is, when Darrell Hammond or Will Ferrell or Dana Carvey did an impersonation of a president, no one assumed it was personal, but because Sarah Palin and I are both women and people think women are meaner to each other, everyone assumed it was personal.”

Power Clothes . . .

Of all the crazy, pinch-me-I’m-dreaming things that have happened to Tina Fey in the last year, by far the best was the day she was interviewed for O magazine. “Oprah came to my apartment,” she says. “Oprah and Gayle were in my apartment, and they stayed for hours. It’s like the most amazing thing that can happen to a white woman in the twenty-first century.” Which brings us around to a discussion of literal power and fashion. Are there any women today who have real power and who aren’t afraid of fashion? She has trouble thinking of any. “How far do you have to go back before women with real power felt like they could wear something that wasn’t an apology for their gender?” She laughs. “You have to go back to, like, Cleopatra.” Finally she says, “Oprah. She dresses. She doesn’t wear a suit every day. She’s feminine. She’s got real power.”

In the first episode of 30 Rock, there’s a funny moment that revolves around Fey donning a power suit to please Alec Baldwin’s character. This is obviously a minor fixation of hers. “When I think of the word power with the word fashion, all I can think of is that color—my least favorite color in the world—that eighties power-blue suit color that businesswomen and politicians still have to wear. I had a roommate once in the early nineties in Chicago, and she had that suit with gold buttons down the front. We would take turns wearing it to job interviews. We thought, These are powerful clothes. It’s a weird position to be in. You look at women who are actually leaders, like Hillary Clinton; what she wears is going to be discussed and scrutinized regardless, but she wears that suit in VOGUE anyway. It’s a way of saying, ‘I’m showing up; I’m being responsible; I’m dressing appropriately for the occasion; but I do not want to call attention to it. I’m taking fashion off the table.’ ”

. . . vs. the Power of Clothes

“I spend most of my time in my daily life trying to be like a fashion noncombatant. My hands are up! I’m not even trying! That said, to talk about the impact of fashion is really interesting. I think so much of it is tied into feminism. I am a post-baby boomer who has been handed a sort of Spice Girls’ version of feminism. We’re supposed to be wearing half-shirts and jumping around. And, you know, maybe that’s not panning out. But you can tell different generations of women by whether or not they wear that Hillary Clinton blue power suit or the reappropriated Playboy-symbol necklace worn ironically. I think women dress for other women to let them know what their deal is. Because if women were only dressing for men, there would be nothing but Victoria’s Secret. There would be no Dior.”

The Cover

When Mario Testino shot Fey for the cover of VOGUE in December, he told her, “You look like Stephanie Seeeee-mour.” Her favorite moment: “At one point I was posing for him, and he was talking from behind the camera and he was like, ‘You have to fliiiirt, darleeeng. You have to bee-leeve you are wuuuurthy to be on the cover.’ And then at one point he said very quietly, ‘Lift your chin, darling. You are not eighteen.’ I was like, ‘You probably say that to all the 23-year-olds.’ ”

Of the cleavage-baring Prada dress on the cover? “I am a fan of the deep V. These are the things I learned from my friends who are cutter/drapers: I have an hourglass figure; I do have a waist, but I have full hips and I have decent shoulders. So that V is good for me. I have learned enough that I can go to a rack and say, ‘That’s not going to work. That’s going to work.’ So at awards shows, I wear a deep V. Because it makes the triangles go the right way. Not good on me? Spaghetti straps. It looks like when you tie up a roast before you put it in the oven.”

The Big Screen

Next month, Fey stars in the hilarious new comedy Date Night, with Steve Carell. Because the arc of the story takes place over one long, madcap evening in Manhattan, Fey wears the same dress throughout the entire film. A blue dress. “But it’s not my-least-favorite-color blue. It’s darker. It’s an OK blue. I wear it for the whole movie—which means I wore this dress for 57 days in a row. And it was interesting to go into that fitting, when they were trying to find the dress; we tried on like 100 dresses. There were certain things that director Shawn Levy wanted: He wanted it to move well because we were running around the city so much; it had to show up at night, so it couldn’t be a black dress; and it had to be flattering. So I wound up wearing this custom-built dress. I think they made me nine of them. And underneath it I had on a custom-made corset on top of Spanx, which were holding a microphone pack. And I was often aware during filming that Steve Carell could move more easily than I could. And do comedy more easily than I could. And the dress was a real physical impediment. I couldn’t go to the bathroom unassisted. You would think I was making The Marie Antoinette Story, the amount of binding. In my real life I can’t bear anything that is inhibiting—I cannot stand to feel slowed down by clothes at all.” One of the funniest lines in the film is classic Tina Fey—an ad-lib. She and Carell are scrambling up a fire escape and breaking into an apartment. On their way up she shouts, “Everything you’re doing, I’m doing in heels!”

Red Carpet

One night in January I meet Fey for dinner on the Upper West Side. She arrives wearing jeans, a gray T-shirt, a navy cardigan, and a blue, gray, and white-striped scarf. There is a diamond ring on each hand. One is her engagement ring, the other an anniversary gift—worn, she says, “to impress you with my incredible wealth.” We wind up talking about getting ready for awards-show season and all the try-ons and fittings and dress picking that it requires. “When you actually finally have to attend awards shows, you realize how difficult the process is,” she says. “Because every person, no matter who you are—how tall you are, how short you are—some things work on you and some things don’t. I don’t like to wear things that feel like costumes. Whenever I work with a stylist, I always find myself saying the same thing: ‘I want my dress to say, I’m just here from New York.’ That’s why I always end up in black or brown. If I try to wear too much color, I feel like I’m pretending to be from Los Angeles and I’m not getting away with it. But up until the last couple of years I always felt like, Well, I’m really a writer; I’m more about content, so if I really blow it with this dress, it’s fine. Someone once gave me a great piece of advice: When you go to the Oscars, don’t dress like you’re never going to go anywhere again. Don’t take such a big swing.”

When I pull out a collage of eight photographs of Fey on the red carpet in various dresses, she yelps and claps her hands. “Oh, goody!” she says. “A fun game! This is going to make me sound like I know what I’m talking about.” She points to the Carolina Herrera she wore to the Emmys in 2007. “I didn’t know then that you could tape your boobs up with double-stick tape,” she says. “But I did know it by . . . then!” Her finger lands triumphantly on the Roberto Cavalli with a plunging V that she wore to the Golden Globes in 2009. “This is a great dress,” she says of the Kevan Hall with a very fifties silhouette that she wore to the Globes in ’07. “He leaves room for lady parts.” There is an Alberta Ferretti, a Gucci, and then, finally, something that isn’t black or plum or brown or navy—a shimmering, silvery Zac Posen she wore last year to the Oscars. “My girlfriends from work were all pulling for me to wear this one,” she says. “And they were like, ‘Yay! She didn’t wear black!’ It’s very old Hollywood. But it’s tricky because it mermaids a little bit, and that’s tough on a girl with a big can.” She laughs. “They let me keep this one. I think my daughter is going to rock that at her prom.” The corner of her mouth goes up in a self-amused smirk. “Or maybe I’ll just wear it one day to clean the house in. Oh, this old thing?”

A few weeks after our dinner, Fey gets “clobbered” (her word) for the Zac Posen number she wears to the Golden Globes, which took place on a rainy night that called for an umbrella—and inspires more than one critic to remark that she looked like Little Bo Peep. (“Do you think,” she says, “George Clooney will hold a telethon for my dress?”) Will her Oscars dress be more conservative? More daring? “I only know that this dress will have to be ‘fancier’ than a Golden Globes dress,” she says, “but I wouldn’t hold your breath to see me in a four-foot ruffled train with an origami-inspired front. Whatever it is, it will be see-through, because that is my trademark.”